Diethyl-2,2,2-trichlor-1-bnzoylamino-ethylphosphonat | 50966-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Diethyl-2,2,2-trichlor-1-bnzoylamino-ethylphosphonat
• 英文别名: (1-Benzoylamino-2,2,2-trichloro-ethyl)-phosphonic acid diethyl ester；N-(2,2,2-trichloro-1-diethoxyphosphorylethyl)benzamide
• CAS: 50966-08-0
• 化学式: C₁₃H₁₇Cl₃NO₄P
• 分子量: 388.615
• InChiKey: MPCNYOLLUFDJBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diethyl-2,2,2-trichlor-1-bnzoylamino-ethylphosphonat 在 吡啶 、 水 、 氯 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 8.0h， 生成 N-(2,2,2-trichloroacetyl)benzamide
  参考文献：
  名称：

  (N-benzoyl)trichloroacetimidoylphosphonate

  摘要：

  A method for the synthesis of O, O-diethyl (N-benzoyl)trichloroacetimidoylphosphonate (1) by successive reaction of N-(1-diethoxyphosphoryl-2,2-dichlorovinyl)benzamide with Me3SiCl and Cl-2 was proposed. The reaction of phosphonate 1 with R3P follows the [4+1] cycloaddition mechanism to give phosphoranes, whose stability and further transformations are controlled by the nature of R.

  DOI：

  10.1007/bf02494533
• 作为产物：
  描述：

  二乙基亚磷酰氯 、 N-(2,2,2-三氯-1-羟乙基)苯甲酰胺 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以66%的产率得到Diethyl-2,2,2-trichlor-1-bnzoylamino-ethylphosphonat
  参考文献：
  名称：

  三价氯化磷与 N-(α-羟基多卤代烷基)酰胺反应合成 α-(酰基氨基)多卤代烷基磷酰基化合物

  摘要：

  N-(α-羟基多卤代烷基)酰胺与三价氯化磷反应，通过中间体亚磷酸酯或亚膦酸酯的亲磷重排得到α-(酰基氨基)多卤代烷基磷酰基化合物。

  DOI：

  10.1007/bf02495701

文献信息

• Synthesis and in vitro anticytomegalovirus activity of 5-hydroxyalkylamino-1,3-oxazoles derivatives
  作者：Esma R. Abdurakhmanova、Mykhailo Y. Brusnakov、Oleksandr V. Golovchenko、Stepan G. Pilyo、Nataliya V. Velychko、Emma A. Harden、Mark N. Prichard、Scott H. James、Victor V. Zhirnov、Volodymyr S. Brovarets

  DOI：10.1007/s00044-020-02593-6

  日期：2020.9

  A series of derivatives of 5-hydroxyalkylamino-1,3-oxazoles were synthesized. Among these derivatives, 5 compounds have been evaluated for their activities against a normal laboratory human cytomegalovirus (HCMV) strain, AD169, in human foreskin fibroblast (HFF) cells. Bioassays showed that among these, 2 compounds containing a remainder of glucamine exhibited moderate antiviral activity (compounds

  合成了一系列5-羟烷基氨基-1,3-恶唑的衍生物。在这些衍生物中，已经评估了5种化合物在人包皮成纤维细胞（HFF）中对正常实验室人巨细胞病毒（HCMV）株AD169的活性。生物测定法表明，在其中的2种含有剩余葡糖胺的化合物中，抗病毒活性中等（化合物9和15，EC 50  = 5.42 µM，CC 50  > 150 µM，SI 50  > 28，EC 50  = 4.91 µM，CC 50  > 150 µM，SI 50 > 31）。这些化合物之间的区别在于，第一种在第4位包含一个邻苯二甲酰亚胺基团，在第5个位置包含磷酰基，而后者在相应的位置上包含一个苯基基团和一个氰基。但是， 在该试验中，它们的活性远远低于对照药物更昔洛韦（EC 50  = 0.32 µM，CC 50  > 150 µM，SI 50 > 476）。这些和先前获得的数据使我们可以考虑将1,3-恶唑用作合成具有抗HCMV活性的新化合物的有前途的骨架。
• A Facile Synthesis of Derivatives of (1,3,4-Thiadiazol-2-yl)glycine and Its Phosphonyl Analogue
  作者：Vladimir S. Brovarets、Aleksandr V. Golovchenko、Stepan G. Pilyo、Alexander N. Chernega、Boris S. Drach

  DOI：10.1055/s-2003-42458

  日期：——

  The adducts formed by 4-functionally-substituted 2-aryl-5-hydrazino-1,3-oxazoles and aryl isothiocyanates recyclize on heating to produce the hitherto unknown derivatives of (1,3,4-thiadiazol-2-yl)glycine and its phosphonyl analogue.

  由 4-功能取代的 2-芳基-5-肼基-1,3-恶唑和芳基异硫氰酸酯形成的加合物在加热时会发生再循环，生成迄今未知的 (1,3,4-thiadiazol-2-yl)glycine 衍生物及其膦酰类似物。
• Synthesis and properties of methanesulfonyl derivatives of diethyl esters of 5-(hydroxyalkylamino)-1,3-oxazol-4-yl-phosphonic acids
  作者：O. V. Golovchenko、M. Yu. Brusnakov、Yu. O. Shabelko、V. S. Brovarets、R. M. Vydzhak、O. S. Bahrieieva、L. M. Potikha、S. V. Shishkina

  DOI：10.1080/10426507.2023.2251639

  日期：2024.1.2

  A number of [4-(diethoxyphosphoryl)-2-R-1,3-oxazol-5-yl]amino}alkyl methanesulfonates were synthesized and the peculiarities of their reaction with triethylamine were studied. The influence of the...

  合成了多种[4-(二乙氧基磷酰基)-2-R-1,3-恶唑-5-基]氨基}烷基甲磺酸盐，并研究了它们与三乙胺的反应特性。的影响...
• ——
  作者：V. S. Brovarets、R. N. Vydzhak、S. G. Pil'o、K. V. Zyuz'、B. S. Drach

  DOI：10.1023/a:1013982122431

  日期：——

  Treatment of 1-phosphorylated 2,2-dichloroethenylcarboxamides with excess hydrazine hydrate gives in high yields phosphorylated derivatives of 2-alkyl(aryl)-5-hydrazinooxazoles containing the P(O)(OCH3)(2), P(O)(OC2H5)(2), and P+(C6H5)3ClO(4)(-) groups in the 4-position of the ring. The presence of the hydrazine group in these oxazole derivatives was confirmed not only by the spectral data, but also by the reactions with p-toluic aldehyde, p-toluic chloride, and phenyl isothiocyanate.
• N-methyl-D-glucamine-derived 4-substituted 1,3-oxazoles
  作者：E. R. Abdurakhmanova、E. I. Lukashuk、A. V. Golovchenko、S. G. Pil’o、V. S. Brovarets

  DOI：10.1134/s1070363215040143

  日期：2015.4

  Reaction of available derivatives of 1-acylamino-2,2-dichloroacrylic acids as well as diethyl esters of 1-acylamino-2,2,2-trichloroethylphosphonic acids with N-methyl-D-glucamine furnished previously unknown 1,3-oxazole derivatives containing nitrile, ester or phosphonyl groups in the position 4 and N-methyl-D-glucamine residue in the position 5.